7,9,11,13,15,17,19-Heptathiaoctacyclo[12.9.0.02,12.03,10.04,8.05,21.016,23.018,22]tricosa-1(14),2(12),3(10),4(8),5,16(23),18(22),20-octaen-6-yl(trimethyl)silane | 1198158-88-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 7,9,11,13,15,17,19-Heptathiaoctacyclo[12.9.0.02,12.03,10.04,8.05,21.016,23.018,22]tricosa-1(14),2(12),3(10),4(8),5,16(23),18(22),20-octaen-6-yl(trimethyl)silane
• CAS: 1198158-88-1
• 化学式: C₁₉H₁₀S₇Si
• 分子量: 490.836
• InChiKey: KWEZIPOWKGBPAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.61
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  198
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 potassium phosphate 、 二(三叔丁基膦)钯 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以29%的产率得到7,9,11,13,15,17,19-Heptathiaoctacyclo[12.9.0.02,12.03,10.04,8.05,21.016,23.018,22]tricosa-1(14),2(12),3(10),4(8),5,16(23),18(22),20-octaen-6-yl(trimethyl)silane
  参考文献：
  名称：

  Intramolecular Cyclization of Thiophene-Based [7]Helicenes to Quasi-[8]Circulenes

  摘要：

  Intramolecular cyclization in a series of thiophene-based dibromo[7]helicenes (4-6) with different helix Structures is investigated by vacuum pyrolysis, tin- and palladium-mediated C-C bond forming reactions. The product With the cyclic structure of the annelated aromatic rings, which resembles [S]circulene devoid of an atom linkage, is referred to as quasi-[8]circulene. Vacuum pyrolysis of 4 gives insoluble, unidentified products, while 5 and 6 yield the corresponding quasi-[8]circulenes Under similar conditions. Thermogravimetry (TG) and differential scanning calorimetry (DSC) analyses for 4 indicate complex reaction pathways, while those for 5 and 6 show a single process corresponding to a loss of 1 equiv of Br-2 at about 330 degrees C. Pd-mediated reductive cyclization provides quasi-[8]circulenes for all three [7]helicenes, though only 4 gives a good isolated yield. Tributyltin hydride-mediated radical cyclization of 4-6 provides quasi-[8]circulenes In excellent yields, and it is practically insensitive to the helix Structure. Experimental and calculated UV-vis absorption spectra for quasi-[8]circulenes and [8]circulenes are reported. The results suggest that the lack of atom linkage in quasi-[8]circulene does not significantly affect properties and conformation, compared to those for the corresponding [8]circulenes.

  DOI：

  10.1021/jo902030u